Pyrimidine derivatives and processes for the preparation thereof

Details Pyrimidine derivatives and processes for the preparation thereof Pyrimidine derivatives and processes for the preparation thereof

1997-01-23

1998-05-12

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514258, 514275, 544253, 544297, 544326, 544328, 544334, A61K 31505, C07D23902, C07D23970

Patent

active

057505314

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/KR95/00105 filed Aug. 10, 1995.


FIELD OF THE INVENTION

The present invention relates to novel pyrimidine derivatives and pharmaceutically acceptable salts thereof which possess an excellent anti-secretory activity, pharmaceutical compositions containing same as an active ingredient, their novel intermediates, and processes for the preparation thereof.


BACKGROUND OF THE INVENTION

For the treatment of peptic ulcer disease, various drugs such as antacid, anticholinergic agent, H.sub.2 -receptor antagonist and proton pump inhibitor have been used. Recently, the advent of omeprazole useful as a proton pump inhibitor has rekindled research activities in this field.
However, it has been pointed out that the proton pump inhibition by omeprazole is irreversible, which may induce side effects. Accordingly, various attempts to develop a reversible proton pump inhibitor are being actively made. For example, European Patent Nos. 322133 and 404322 disclose quinazoline derivatives, European Patent No. 259174 describes quinoline derivatives, and WO 91/13337 offers pyrimidine derivatives, as a reversible proton pump inhibitor. Further, the present inventors have also reported quinazoline derivatives in WO 94/14795.


SUMMARY OF THE INVENTION

The present inventors have carried out extensive research to develop a reversible proton pump inhibitor with improved efficacy; and, as a result, have discovered that pyrimidine derivatives having a tetrahydroisoquinoline group at the 2- or 4-position of the pyrimidine nucleus exhibit excellent proton pump inhibition effects and possess the ability to attain a reversible proton pump inhibition.
Accordingly, it is a primary object of the present invention to provide novel pyrimidine derivatives having a tetrahydroisoquinoline group at the 2- or 4-position of the pyrimidine nucleus, and pharmaceutically acceptable salts thereof.
It is another object of the present invention to provide processes for preparing said compounds.
It is a further object of the present invention to provide pharmaceutical compositions containing same as active ingredients.
It is still another object of the invention to provide novel intermediate compounds useful for the preparation of the novel pyrimidine derivatives.


DETAILED DESCRIPTION OF THE INVENTION

In accordance with the present invention, there are provided novel pyrimidine derivative compounds of formulae (I-1) and (I-2) inclusive of pharmaceutically acceptable salts thereof: ##STR4## wherein: R.sub.4 and R.sub.5, which may be the same or different, are independently hydrogen or a C.sub.1 -C.sub.3 alkyl group, or jointly form a cyclopentyl or cyclohexyl ring; ##STR5## wherein R.sub.1 and R.sub.2 are, independently of each other, hydrogen or a C.sub.1 -C.sub.3 alkyl group, and R.sub.3 is hydrogen, a C.sub.1 -C.sub.3 alkyl group or a halogen; and (III-2) ##STR6## wherein R.sub.6 is hydrogen or a C.sub.1 -C.sub.3 alkyl group.
Among the compounds of the present invention, preferred are those wherein: R.sub.1, R.sub.2 and R.sub.6 are independently hydrogen or a methyl group; R.sub.3 is hydrogen or a fluorine; and R.sub.4 and R.sub.5, which may be the same or different, are independently hydrogen or a C.sub.1 -C.sub.3 alkyl group, or jointly form a cyclopentyl or cyclohexyl ring.
Particularly, preferred compounds of the present invention are: 2-yl)pyrimidine hydrochloride; quinolin-2-yl)pyrimidine hydrochloride; mino)pyrimidine hydrochloride; 2-yl)pyrimidine hydrochloride; uinolin-2-yl)pyrimidine hydrochloride; -yl)pyrimidine hydrochloride; -yl)pyrimidine hydrochloride; -yl)pyrimidine hydrochloride; 2-yl)-6-propylpyrimidine hydrochloride; mino)pyrimidine hydrochloride; ropylpyrimidine hydrochloride; oisoquinolin-2-yl)pyrimidine hydrochloride; hydroisoquinolin-2-yl)pyrimidine hydrochloride; hydroisoquinolin-2-yl)pyrimidine hydrochloride; lin-2-yl)pyrimidine hydrochloride; uinolin-2-yl)pyrimidine hydrochloride; uinolin-2-yl)pyrimidine hydrochloride; lin-2-yl)pyrimidine hydrochloride; uinolin-2-yl)pyrimidine hydrochlorid

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